CA2475586A1 - Novel boronate esters - Google Patents
Novel boronate esters Download PDFInfo
- Publication number
- CA2475586A1 CA2475586A1 CA002475586A CA2475586A CA2475586A1 CA 2475586 A1 CA2475586 A1 CA 2475586A1 CA 002475586 A CA002475586 A CA 002475586A CA 2475586 A CA2475586 A CA 2475586A CA 2475586 A1 CA2475586 A1 CA 2475586A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- aryl
- carbons
- aralkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical class OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 title claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 10
- 125000003118 aryl group Chemical group 0.000 claims abstract 10
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 8
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract 3
- FJLGEFLZQAZZCD-MCBHFWOFSA-N (3R,5S)-fluvastatin Chemical compound C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 FJLGEFLZQAZZCD-MCBHFWOFSA-N 0.000 claims abstract 2
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims abstract 2
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 claims abstract 2
- 229960005370 atorvastatin Drugs 0.000 claims abstract 2
- 230000015572 biosynthetic process Effects 0.000 claims abstract 2
- 229960005110 cerivastatin Drugs 0.000 claims abstract 2
- SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 claims abstract 2
- 229960003765 fluvastatin Drugs 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 229960002797 pitavastatin Drugs 0.000 claims abstract 2
- VGYFMXBACGZSIL-MCBHFWOFSA-N pitavastatin Chemical compound OC(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 VGYFMXBACGZSIL-MCBHFWOFSA-N 0.000 claims abstract 2
- 229960000672 rosuvastatin Drugs 0.000 claims abstract 2
- BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 claims abstract 2
- 238000003786 synthesis reaction Methods 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 13
- 238000000034 method Methods 0.000 claims 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical group C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 3
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims 2
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 claims 2
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- 239000003377 acid catalyst Substances 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 claims 1
- CABVTRNMFUVUDM-VRHQGPGLSA-N (3S)-3-hydroxy-3-methylglutaryl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C[C@@](O)(CC(O)=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 CABVTRNMFUVUDM-VRHQGPGLSA-N 0.000 abstract 1
- 239000002532 enzyme inhibitor Substances 0.000 abstract 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical class CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Pyrrole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The present invention relates to optically active dihydroxy hexanoate derivatives, boronate esters of formula IIa which are useful intermediates for the synthesis of HMG-CoA enzyme inhibitors like atorvastatin, cerivastatin, rosuvastatin, pitavastatin, fluvastatin.
Claims (9)
1. The product of formula IIa wherein Ar = unsubstituted or substituted aryl or heteroaryl R3 = alkyl from 1 to 8 carbons, aryl or aralkyl R4 = O, OH, CN or a halogen and a = single bond or double bond
2. The product as claimed in claim 1 wherein said product is a compound of formula II
wherein Ar = unsubstituted or substituted aryl or heteroaryl R3 = alkyl from 1 to 8 carbons, aryl or aralkyl
wherein Ar = unsubstituted or substituted aryl or heteroaryl R3 = alkyl from 1 to 8 carbons, aryl or aralkyl
3. A process for the manufacture of compounds of formula II
Ar = unsubstituted, or substituted aryl or heteroaryl R3 = alkyl from 1 to 8 carbons, aryl or aralkyl which comprises of:
(a) reacting compound of formula III with the anion of tertiary butyl acetate to give a compound of formula IV, where G is tetrahydropyranyl, tert-butydimethyl silyl or trityl and R3 is alkyl from 1 to 8 carbons, aryl or aralkyl, (b) subjecting compound of formula IV to reduction to give a compound of formula V, where G is tetrahydropyranyl, tert-butyldimethyl silyl or trityl and R3 is alkyl from 1 to 8 carbons, aryl or aralkyl, (c) protecting the compound of formula V with ArB(OH)2 to give a compound of formula VI, where Ar is unsubstituted or substituted aryl or heteroaryl, G is tetrahydropyranyl, tert-butyldimethyl silyl or trityl and R3 is alkyl from 1 to 8 carbons, aryl or aralkyl, and (f) deprotection of the compound of formula VI using mild acid catalyst to give a compound of formula II.
Ar = unsubstituted, or substituted aryl or heteroaryl R3 = alkyl from 1 to 8 carbons, aryl or aralkyl which comprises of:
(a) reacting compound of formula III with the anion of tertiary butyl acetate to give a compound of formula IV, where G is tetrahydropyranyl, tert-butydimethyl silyl or trityl and R3 is alkyl from 1 to 8 carbons, aryl or aralkyl, (b) subjecting compound of formula IV to reduction to give a compound of formula V, where G is tetrahydropyranyl, tert-butyldimethyl silyl or trityl and R3 is alkyl from 1 to 8 carbons, aryl or aralkyl, (c) protecting the compound of formula V with ArB(OH)2 to give a compound of formula VI, where Ar is unsubstituted or substituted aryl or heteroaryl, G is tetrahydropyranyl, tert-butyldimethyl silyl or trityl and R3 is alkyl from 1 to 8 carbons, aryl or aralkyl, and (f) deprotection of the compound of formula VI using mild acid catalyst to give a compound of formula II.
4. A process as claimed in claim 3 wherein ArB(OH)2 is boronic acid.
5. A process as claimed in claim 3 wherein compound of formula II
is oxidized to a compound of formula VIII, where R3 is alkyl from 1 to 8 carbons, aryl or aralkyl and Ar is unsubstituted or substituted aryl or heteroaryl using pyridinium chloro chromate or DMSO/oxalyl chloride.
is oxidized to a compound of formula VIII, where R3 is alkyl from 1 to 8 carbons, aryl or aralkyl and Ar is unsubstituted or substituted aryl or heteroaryl using pyridinium chloro chromate or DMSO/oxalyl chloride.
6. A process as claimed in Claim 3 wherein compound of formula II
is further converted to a compound of formula IX, where R3 is alkyl from 1 to 8 carbons, aryl or aralkyl, Ar is unsubstituted or substituted aryl or heteroaryl and X is a halogen.
is further converted to a compound of formula IX, where R3 is alkyl from 1 to 8 carbons, aryl or aralkyl, Ar is unsubstituted or substituted aryl or heteroaryl and X is a halogen.
7. A process as claimed in claim 6 wherein compound of formula II is converted to compound of formula IX by reacting compound of formula II with aqueous HBr solution or by reaction with triphenyl phosphine and CBr4.
8. A process as claimed in claim 6 or 7 wherein compound of formula IX is further converted to a compound of formula VII, where R3 is alkyl from 1 to 8 carbons, aryl or aralkyl, Ar is unsubstituted or substituted aryl or heteroaryl.
9. The product as claimed in claim 1, used in the synthesis of atorvastatin, cerivastatin, pitavastatin, fluvastatin or rosuvastatin.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IN2002/000032 WO2003070733A1 (en) | 2002-02-25 | 2002-02-25 | Novel boronate esters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2475586A1 true CA2475586A1 (en) | 2003-08-28 |
| CA2475586C CA2475586C (en) | 2011-07-05 |
Family
ID=27742233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2475586A Expired - Fee Related CA2475586C (en) | 2002-02-25 | 2002-02-25 | Novel boronate esters |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US7301046B2 (en) |
| EP (1) | EP1478650B1 (en) |
| JP (1) | JP4139334B2 (en) |
| KR (1) | KR100598079B1 (en) |
| AT (1) | ATE444299T1 (en) |
| AU (1) | AU2002241235B2 (en) |
| BR (1) | BR0215602A (en) |
| CA (1) | CA2475586C (en) |
| CZ (1) | CZ2004863A3 (en) |
| DE (1) | DE60233899D1 (en) |
| DK (1) | DK1478650T3 (en) |
| ES (1) | ES2332881T3 (en) |
| HR (1) | HRP20040888B1 (en) |
| HU (1) | HUP0500125A3 (en) |
| IL (1) | IL163333A (en) |
| NO (1) | NO20043223L (en) |
| NZ (1) | NZ534688A (en) |
| PT (1) | PT1478650E (en) |
| RO (1) | RO122095B1 (en) |
| SK (1) | SK288093B6 (en) |
| WO (1) | WO2003070733A1 (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0011120D0 (en) * | 2000-05-09 | 2000-06-28 | Avecia Ltd | Process |
| NL1015744C2 (en) | 2000-07-19 | 2002-01-22 | Dsm Nv | Process for the preparation of 2- (6-substituted-1,3-dioxan-4-yl) acetic acid derivatives. |
| EP1323717A1 (en) * | 2001-12-27 | 2003-07-02 | Dsm N.V. | Process for the preparation of 2-(6-Substituted-1,3-Dioxane-4-yL) acetic acid derivatives |
| DK1478650T3 (en) | 2002-02-25 | 2010-01-25 | Biocon Ltd | New boronate esters |
| CN101512004A (en) * | 2006-07-19 | 2009-08-19 | 密歇根州州立大学托管委员会 | Microbial synthesis of D-1,2,4-butanetriol |
| EP2066788B1 (en) | 2006-10-02 | 2014-07-23 | Codexis, Inc. | Compositions and methods for producing stereoisomerically pure statins and synthetic intermediates therefor |
| KR100933172B1 (en) | 2007-11-30 | 2009-12-21 | 씨제이제일제당 (주) | Improved preparation of atorvastatin calcium salt |
| KR101339648B1 (en) * | 2012-05-10 | 2013-12-09 | (주) 에프엔지리서치 | Novel atorvastatin intermediates and method for synthesizing atorvastatin by using atorvastatin intermediates |
| KR101292743B1 (en) * | 2012-05-17 | 2013-08-02 | (주) 에프엔지리서치 | Novel statins intermediates and method for synthesizing pitavastain, rosuvastatin, cerivastatin and fluvastatin by using statins intermediates |
| KR101528359B1 (en) * | 2013-04-24 | 2015-06-15 | (주) 성운파마코피아 | Novel boronate ether intermediates for preparation of statin compounds, preparation method thereof and preparation method of statin compounds using said boronate ether intermediates |
| CN108033899B (en) * | 2017-12-06 | 2020-04-10 | 浙江科技学院 | Preparation method of (R) -6-cyano-5-hydroxy-3-carbonyl hexanoate tert-butyl ester |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4474034A (en) | 1982-09-23 | 1984-10-02 | Avery Jr Richard J | Refrigerant accumulator and charging apparatus and method for vapor-compression refrigeration system |
| DE3741509A1 (en) * | 1987-12-08 | 1989-06-22 | Hoechst Ag | METHOD FOR PRODUCING OPTICALLY ACTIVE 3-DESMETHYLMEVALONIC ACID DERIVATIVES AND INTERMEDIATE PRODUCTS |
| EP0579370B1 (en) | 1992-06-10 | 2000-08-16 | Chisso Corporation | An optically active 1,5-disubstituted-2,4-0-isoproylidene-2,4-dihydroxypentane and a process for producing the same |
| ATE158579T1 (en) | 1992-07-02 | 1997-10-15 | Hoechst Ag | METHOD FOR PRODUCING (3R,5S)6-HYDROXY-3,5-0-ISOPROPYLIDENE-3,5-DIHYDROXY-HEXANOID-TERT-BUTYL ESTER |
| US5481009A (en) * | 1993-08-09 | 1996-01-02 | Fujirebio Inc. | Methods of producing carboxylic acid ester derivatives and intermediates for use in the methods |
| US5998633A (en) * | 1996-07-29 | 1999-12-07 | Warner-Lambert Company | Process for the synthesis of protected esters of (S)-3,4-dihydroxybutyric acid |
| JPH11171850A (en) * | 1997-12-12 | 1999-06-29 | Kanegafuchi Chem Ind Co Ltd | Production of butyric ester derivative |
| AU2000254249A1 (en) | 2000-03-28 | 2001-10-08 | Biocon India Limited | Synthesis of (r-(r*,r*))-2-(4-fluorophenyl)-beta,delta-dihydroxy-5-(1- |
| WO2002057229A1 (en) | 2001-01-19 | 2002-07-25 | Biocon India Limited | FORM V CRYSTALLINE [R-(R*,R*)]-2-(4-FLUOROPHENYL)-ß,$G(D)-DIHYDROXY-5-(1-METHYLETHYL)-3-PHENYL-4-[(PHENYLAMINO)CARBONYL]-1H-PYRROLE-1- HEPTANOIC ACID HEMI CALCIUM SALT. (ATORVASTATIN) |
| DK1478650T3 (en) * | 2002-02-25 | 2010-01-25 | Biocon Ltd | New boronate esters |
-
2002
- 2002-02-25 DK DK02707083.8T patent/DK1478650T3/en active
- 2002-02-25 DE DE60233899T patent/DE60233899D1/en not_active Expired - Lifetime
- 2002-02-25 NZ NZ534688A patent/NZ534688A/en not_active IP Right Cessation
- 2002-02-25 BR BR0215602-4A patent/BR0215602A/en not_active Application Discontinuation
- 2002-02-25 KR KR1020047012639A patent/KR100598079B1/en not_active IP Right Cessation
- 2002-02-25 WO PCT/IN2002/000032 patent/WO2003070733A1/en active IP Right Grant
- 2002-02-25 PT PT02707083T patent/PT1478650E/en unknown
- 2002-02-25 HU HU0500125A patent/HUP0500125A3/en unknown
- 2002-02-25 RO ROA200400728A patent/RO122095B1/en unknown
- 2002-02-25 CA CA2475586A patent/CA2475586C/en not_active Expired - Fee Related
- 2002-02-25 SK SK305-2004A patent/SK288093B6/en not_active IP Right Cessation
- 2002-02-25 AT AT02707083T patent/ATE444299T1/en not_active IP Right Cessation
- 2002-02-25 EP EP02707083A patent/EP1478650B1/en not_active Expired - Lifetime
- 2002-02-25 AU AU2002241235A patent/AU2002241235B2/en not_active Ceased
- 2002-02-25 ES ES02707083T patent/ES2332881T3/en not_active Expired - Lifetime
- 2002-02-25 CZ CZ2004863A patent/CZ2004863A3/en unknown
- 2002-02-25 JP JP2003569640A patent/JP4139334B2/en not_active Expired - Fee Related
- 2002-02-25 US US10/505,528 patent/US7301046B2/en not_active Expired - Fee Related
-
2004
- 2004-07-29 NO NO20043223A patent/NO20043223L/en not_active Application Discontinuation
- 2004-08-03 IL IL163333A patent/IL163333A/en not_active IP Right Cessation
- 2004-08-23 US US10/923,934 patent/US7238826B2/en not_active Expired - Fee Related
- 2004-09-24 HR HR20040888 patent/HRP20040888B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2475586C (en) | 2011-07-05 |
| NO20043223L (en) | 2004-09-28 |
| AU2002241235A1 (en) | 2003-09-09 |
| PT1478650E (en) | 2010-01-04 |
| JP2005518427A (en) | 2005-06-23 |
| US20050154213A1 (en) | 2005-07-14 |
| DE60233899D1 (en) | 2009-11-12 |
| DK1478650T3 (en) | 2010-01-25 |
| US7238826B2 (en) | 2007-07-03 |
| ES2332881T3 (en) | 2010-02-15 |
| BR0215602A (en) | 2004-12-07 |
| HRP20040888A2 (en) | 2005-04-30 |
| ATE444299T1 (en) | 2009-10-15 |
| CZ2004863A3 (en) | 2004-12-15 |
| NZ534688A (en) | 2005-04-29 |
| IL163333A (en) | 2009-05-04 |
| HUP0500125A2 (en) | 2005-04-28 |
| EP1478650A4 (en) | 2008-02-13 |
| HRP20040888B1 (en) | 2012-12-31 |
| US20060040898A1 (en) | 2006-02-23 |
| US7301046B2 (en) | 2007-11-27 |
| RO122095B1 (en) | 2008-12-30 |
| KR100598079B1 (en) | 2006-07-07 |
| JP4139334B2 (en) | 2008-08-27 |
| HUP0500125A3 (en) | 2008-03-28 |
| EP1478650A1 (en) | 2004-11-24 |
| SK288093B6 (en) | 2013-07-02 |
| SK3052004A3 (en) | 2005-02-04 |
| KR20040084915A (en) | 2004-10-06 |
| AU2002241235B2 (en) | 2009-04-23 |
| EP1478650B1 (en) | 2009-09-30 |
| WO2003070733A1 (en) | 2003-08-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20160225 |